LANOPEPDEN MESYLATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H34FN7O4.CH4O3S
Molecular Weight	575.654
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CS(O)(=O)=O.[H][C@]12COCCN1CCN(C2)C3=C(F)C(NNC(=O)[C@H](CC4CCCC4)CN(O)C=O)=NC(C)=N3

InChI

InChIKey=UNGNACZMQRGYNV-URBRKQAFSA-N

InChI=1S/C22H34FN7O4.CH4O3S/c1-15-24-20(19(23)21(25-15)29-7-6-28-8-9-34-13-18(28)12-29)26-27-22(32)17(11-30(33)14-31)10-16-4-2-3-5-16;1-5(2,3)4/h14,16-18,33H,2-13H2,1H3,(H,27,32)(H,24,25,26);1H3,(H,2,3,4)/t17-,18+;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C22H34FN7O4
Molecular Weight	479.5483
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	CH4O3S
Molecular Weight	96.106
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/mesh/67583947 | https://www.ncbi.nlm.nih.gov/pubmed/21918031 | https://www.ncbi.nlm.nih.gov/pubmed/23403431

LANOPEPDEN is an inhibitor of peptide deformylase, a bacterial enzyme required for protein maturation. It was in development for the treatment of complicated bacterial skin infection and hospitalized community-acquired pneumonia.

Approval Year

PubMed

Title	Date	PubMed
Antibiotics in development targeting protein synthesis.	2011 Dec	22191530
Determination of disk diffusion and MIC quality control ranges for GSK1322322, a novel peptide deformylase inhibitor.	2011 Nov	21918031
Single-dose safety, tolerability, and pharmacokinetics of the antibiotic GSK1322322, a novel peptide deformylase inhibitor.	2013 May	23403431
Comparative analysis of the antibacterial activity of a novel peptide deformylase inhibitor, GSK1322322.	2013 May	23478958

Patents

Sample Use Guides

In Vitro Use Guide

Lanopepden (GSK1322322) had an MIC90 of 1 μg/ml against M. catarrhalis and 4 μg/ml against H. influenzae, with 88.8% of beta-lactamase-positive strains showing growth inhibition at that concentration. All S. pneumoniae strains were inhibited by ≤ 4 μg/ml of GSK1322322, with an MIC90 of 2 μg/ml. GSK1322322 was very potent against S. pyogenes strains, with an MIC90 of 0.5 μg/ml, irrespective of their macrolide resistance phenotype. It was also active against S. aureus strains regardless of their susceptibility to methicillin, macrolides, or levofloxacin, with an MIC90 of 4 μg/ml in all cases.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 11:03:17 GMT 2023` Edited by `admin` on `Sat Dec 16 11:03:17 GMT 2023`
Record UNII	YW25HPP501
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LANOPEPDEN MESYLATE

Official Name

English

GSK-1322322 MESYLATE SALT

Code

English

CYCLOPENTANEPROPANOIC ACID, .ALPHA.-((FORMYLHYDROXYAMINO)METHYL)-, (.ALPHA.R)-, 2-(5-FLUORO-6-((9AS)-HEXAHYDROPYRAZINO(2,1-C)(1,4)OXAZIN-8(1H)-YL)-2-METHYL-4-PYRIMIDINYL)HYDRAZIDE, METHANESULFONATE (1:1)

Systematic Name

English

GSK1322322J

Code

English

LANOPEPDEN MESYLATE [USAN]

Common Name

English

GSK1322322 MESYLATE SALT

Code

English

GSK-1322322J

Code

English

Lanopepden mesilate [WHO-DD]

Common Name

English

LANOPEPDEN MESILATE

Common Name

English

GSK-1322322 MESYLATE

Common Name

English

Code System Code Type Description

ChEMBL

CHEMBL3301608